I ran across Chocolatey years ago when Scott Hanselman wrote about it in his power tool list. At the time, I wasn’t in need of the tool, but I thought it was cool and tried it. I was hooked.

In fact, the next year I got two different laptops, and using chocolatey, I was up and running in an hour, being productive. As I found software I needed, I just grabbed a package from Chocolatey and continued working while it installed. This was way, way easier than anything I’ve done outside of a Linux environment.

Getting Started

The first thing to do in order to use Chocolatey is go to the install page and run the PowerShell command in an administrative command prompt. That’s easy to do.

NOTE: This is a security change, so I’d do this on dev and client machines, not production boxes.

Once you’ve installed and enabled Chocolatey, the next step is to use it. When I have a new machine, the first thing I do is get Dropbox. The reason is that Dropbox has my passwords and my Chocolatey script. This is as simple as opening your command window and typing

choco install dropbox

This installs and I log in and start downloading my Dropbox to the local machine. While this is working, I may open a second command window and do this

choco install googlechrome

Since this is a staple for me on any machine. I do usually add FireFox as well, but Chrome is the first browser for me.

There are lots of packages available, and you can search for them. Once you get used to the tool, you’ll find yourself guessing at names to install things.

That’s it.

Just in Time Installs

I have a batch file with a lot of “choco install xx” statements, but I don’t worry about making it too complete. In fact, I try to keep this to a minimal number of software applications because I do change my habits over time.

I get the software I need, as I need it. When I built my last machine, I was still using cmd.exe. However, I decided to move to ConEmu on one machine and used “choco install conemu” to get the software on one machine. I liked the tool and a few months later I needed it on another machine, so I used chocolatey to just get it. While working, ConEmu installed in the background, and I could use it a few minutes later.

The same thing with most other software. Greenshot, Visual Studio Code, many things I need are just easier to install now. If I need something, I call a package and it installs.

Exceptions

There are some exceptions. Notably for me, Redgate products aren’t up there, so I have to download those separately. We also use O365 for Office, and that’s a separate install. In fact, if you use media, you’ll have to uninstall and reinstall from the o365 site. SQL Server also requires a separate download and install.

Convenience

The main reason I use chocolatey is that is saves time. I don’t hunt through Google and websites for download links, I don’t next…next…next for installs. I have ConEmu running, so a CTRL+~, pick my ConEmu window and choco install what I need, letting this run in the background while I task switch to something else.

This might not be for everyone, but I’ve found it very convenient and easy to use. Moving to chocolatey allows me to start treating laptops and desktops like cattle (with Evernote, Dropbox, OneDrive, etc.) and not be too concerned about the effort to rebuild or restore a system.

My next thought is to get some of the tools I need, like test SQL instances, into containers, and perhaps being able to back these up and restore them even quicker than I can today.

I tried Chocolatey just because you recommended it so highly, and I love it. My home set up is nearly exclusively Linux these days (blame the Raspberry Pi), and this works in a very similar way to Apt/Apt-Get and makes adding new software packages easy, Add Windows Quake Console, configured to use PowerShell, for an even easier time.